[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5483/BMBRep.2012.45.8.161

Analysis and role of oligosaccharides in milk

Ruhaak, L. Renee (Department of Chemistry, University of California Davis)
Lebrilla, Carlito B. (Department of Chemistry, University of California Davis)

Publication Information

BMB Reports / v.45, no.8, 2012 , pp. 442-451 More about this Journal

Abstract

Milk is an important fluid in glycobiology because it contains a number of short carbohydrate chains either free or as glycoconjugates. These compounds as a class are the most abundant component and benefit the infant by developing and maintaining the infant's gut flora. New and emerging methods for oligosaccharide analysis have been developed to study milk. These methods allow for the rapid profiling of oligosaccharide mixtures with quantitation. With these tools, the role of oligosaccharide in milk is being understood. They further point to how oligosaccharide analysis can be performed, which until now has been very difficult and have lagged significantly those of other biopolymers.

Keywords

Analysis; Bacterial consumption; High performance liquid chromatography; Lewis blood group; Mass spectrometry; Milk oligosaccharides; Secretor status;

Citations & Related Records

Times Cited By Web Of Science : 1 (Related Records In Web of Science)

Reference

1	Ruhaak, L. R., Huhn, C., Waterreus, W. J., de Boer, A. R., Neususs, C., Hokke, C. H., Deelder, A. M. and Wuhrer, M. (2008) Hydrophilic interaction chromatography-based high-throughput sample preparation method for N-glycan analysis from total human plasma glycoproteins. Anal. Chem. 80, 6119-6126. DOI ScienceOn
2	Shen, Z., Warren, C. D. and Newburg, D. S. (2000) High-performance capillary electrophoresis of sialylated oligosaccharides of human milk. Anal. Biochem. 279, 37-45. DOI ScienceOn
3	Bao, Y., Zhu, L. and Newburg, D. S. (2007) Simultaneous quantification of sialyloligosaccharides from human milk by capillary electrophoresis. Anal. Biochem. 370, 206-214. DOI ScienceOn
4	Albrecht, S., Schols, H. A., van den Heuvel, E. G., Voragen, A. G. and Gruppen, H. (2010) CE-LIF-MS n profiling of oligosaccharides in human milk and feces of breast-fed babies. Electrophoresis 31, 1264-1273. DOI ScienceOn
5	Albrecht, S., Schols, H. A., van den Heuvel, E. G., Voragen, A. G. and Gruppen, H. (2011) Occurrence of oligosaccharides in feces of breast-fed babies in their first six months of life and the corresponding breast milk. Carbohydr. Res. 346, 2540-2550. DOI ScienceOn
6	Albrecht, S., Schols, H. A., van Zoeren, D., van Lingen, R. A., Groot Jebbink, L. J., van den Heuvel, E. G., Voragen, A. G. and Gruppen, H. (2011) Oligosaccharides in feces of breast- and formula-fed babies. Carbohydr. Res. 346, 2173-2181. DOI ScienceOn
7	Huhn, C., Ramautar, R., Wuhrer, M. and Somsen, G. W. (2010) Relevance and use of capillary coatings in capillary electrophoresis-mass spectrometry. Anal. Bioanal. Chem. 396, 297-314. DOI
8	Ruhaak, L. R., Zauner, G., Huhn, C., Bruggink, C., Deelder, A. M. and Wuhrer, M. (2010) Glycan labeling strategies and their use in identification and quantification. Anal. Bioanal. Chem. 397, 3457-3481. DOI
9	Costello, C. E., Contado-Miller, J. M. and Cipollo, J. F. (2007) A glycomics platform for the analysis of permethylated oligosaccharide alditols. J. Am. Soc. Mass Spectrom. 18, 1799-1812. DOI ScienceOn
10	Asakuma, S., Urashima, T., Akahori, M., Obayashi, H., Nakamura, T., Kimura, K., Watanabe, Y., Arai, I. and Sanai, Y. (2008) Variation of major neutral oligosaccharides levels in human colostrum. Eur. J. Clin. Nutr. 62, 488-494. DOI ScienceOn
11	Sumiyoshi, W., Urashima, T., Nakamura, T., Arai, I., Saito, T., Tsumura, N., Wang, B., Brand-Miller, J., Watanabe, Y. and Kimura, K. (2003) Determination of each neutral oligosaccharide in the milk of Japanese women during the course of lactation. Br. J. Nutr. 89, 61-69. DOI ScienceOn
12	Leo, F., Asakuma, S., Fukuda, K., Senda, A. and Urashima, T. (2010) Determination of sialyl and neutral oligosaccharide levels in transition and mature milks of Samoan women, using anthranilic derivatization followed by reverse phase high performance liquid chromatography. Biosci. Biotechnol. Biochem. 74, 298-303. DOI ScienceOn
13	Leo, F., Asakuma, S., Nakamura, T., Fukuda, K., Senda, A. and Urashima, T. (2009) Improved determination of milk oligosaccharides using a single derivatization with anthranilic acid and separation by reversed-phase high-performance liquid chromatography. J. Chrom. A 1216, 1520-1523. DOI ScienceOn
14	Royle, L., Campbell, M. P., Radcliffe, C. M., White, D. M., Harvey, D. J., Abrahams, J. L., Kim, Y. G., Henry, G. W., Shadick, N. A., Weinblatt, M. E., Lee, D. M., Rudd, P. M. and Dwek, R. A. (2008) HPLC-based analysis of serum N-glycans on a 96-well plate platform with dedicated database software. Anal. Biochem. 376, 1-12. DOI ScienceOn
15	Marcobal, A., Barboza, M., Froehlich, J. W., Block, D. E., German, J. B., Lebrilla, C. B. and Mills, D. A. (2010) Consumption of human milk oligosaccharides by gut-related microbes. J. Agric. Food Chem. 58, 5334-5340. DOI ScienceOn
16	Ninonuevo, M. R., Ward, R. E., LoCascio, R. G., German, J. B., Freeman, S. L., Barboza, M., Mills, D. A. and Lebrilla, C. B. (2007) Methods for the quantitation of human milk oligosaccharides in bacterial fermentation by mass spectrometry. Anal. Biochem. 361, 15-23. DOI ScienceOn
17	O'hara, A. M. and Shanahan, F. (2006) The gut flora as a forgotten organ. EMBO Rep. 7, 688-693. DOI ScienceOn
18	Stahl, B., Thurl, S., Zeng, J., Karas, M., Hillenkamp, F., Steup, M. and Sawatzki, G. (1994) Oligosaccharides from human milk as revealed by matrix-assisted laser desorption/ ionization mass spectrometry. Anal. Biochem. 223, 218-226. DOI ScienceOn
19	Locascio, R. G., Ninonuevo, M. R., Kronewitter, S. R., Freeman, S. L., German, J. B., Lebrilla, C. B. and Mills, D. A. (2009) A versatile and scalable strategy for glycoprofiling bifidobacterial consumption of human milk oligosaccharides. Microb. Biotechnol. 2, 333-342. DOI ScienceOn
20	Zauner, G., Deelder, A. M. and Wuhrer, M. (2011) Recent advances in hydrophilic interaction liquid chromatography (HILIC) for structural glycomics. Electrophoresis 32, 3456-3466. DOI ScienceOn
21	Wuhrer, M., de Boer, A. R. and Deelder, A. M. (2009) Structural glycomics using hydrophilic interaction chromatography (HILIC) with mass spectrometry. Mass Spectrom. Rev. 28, 192-206. DOI ScienceOn
22	Ruhaak, L. R., Deelder, A. M. and Wuhrer, M. (2009) Oligosaccharide analysis by graphitized carbon liquid chromatography-mass spectrometry. Anal. Bioanal. Chem. 394, 163-174. DOI
23	Pabst, M. and Altmann, F. (2011) Glycan analysis by modern instrumental methods. Proteomics 11, 631-643. DOI ScienceOn
24	Marcobal, A. and Sonnenburg, J. L. (2012) Human milk oligosaccharide consumption by intestinal microbiota. Clin. Microbiol. Infect. 18(Suppl 4), 12-15. DOI ScienceOn
25	Coppa, G. V., Zampini, L., Galeazzi, T., Facinelli, B., Ferrante, L., Capretti, R. and Orazio, G. (2006) Human milk oligosaccharides inhibit the adhesion to Caco-2 cells of diarrheal pathogens: Escherichia coli, Vibrio cholerae, and Salmonella fyris. Pediatr. Res. 59, 377-382. DOI ScienceOn
26	Ruiz-Palacios, G. M., Cervantes, L. E., Ramos, P., Chavez- Munguia, B. and Newburg, D. S. (2003) Campylobacter jejuni binds intestinal H(O) antigen (Fuc alpha 1, 2Gal beta 1, 4GlcNAc), and fucosyloligosaccharides of human milk inhibit its binding and infection. J. Biol. Chem. 278, 14112-14120. DOI ScienceOn
27	Morrow, A. L., Ruiz-Palacios, G. M., Altaye, M., Jiang, X., Guerrero, M. L., Meinzen-Derr, J. K., Farkas, T., Chaturvedi, P., Pickering, L. K. and Newburg, D. S. (2004) Human milk oligosaccharides are associated with protection against diarrhea in breast-fed infants. J. Pediatr. 145, 297-303. DOI ScienceOn
28	Marcobal, A., Barboza, M., Sonnenburg, E. D., Pudlo, N., Martens, E. C., Desai, P., Lebrilla, C. B., Weimer, B. C., Mills, D. A., German, J. B. and Sonnenburg, J. L. (2011) Bacteroides in the infant gut consume milk oligosaccharides via mucus-utilization pathways. Cell Host. Microbe. 10, 507-514. DOI ScienceOn
29	Sela, D. A., Li, Y., Lerno, L., Wu, S., Marcobal, A. M., German, J. B., Chen, X., Lebrilla, C. B. and Mills, D. A. (2011) An infant-associated bacterial commensal utilizes breast milk sialyloligosaccharides. J. Biol. Chem. 286, 11909-11918. DOI ScienceOn
30	LoCascio, R. G., Ninonuevo, M. R., Freeman, S. L., Sela, D. A., Grimm, R., Lebrilla, C. B., Mills, D. A. and German, J. B. (2007) Glycoprofiling of bifidobacterial consumption of human milk oligosaccharides demonstrates strain specific, preferential consumption of small chain glycans secreted in early human lactation. J. Agric. Food Chem. 55, 8914-8919. DOI
31	German, J. B., Freeman, S. L., Lebrilla, C. B. and Mills, D. A. (2008) Human milk oligosaccharides: evolution, structures and bioselectivity as substrates for intestinal bacteria. Nestle Nutr. Workshop Ser. Pediatr. Program 62, 205-218. DOI ScienceOn
32	Osthoff, G., Dickens, L., Urashima, T., Bonnet, S. L., Uemura, Y. and van der Westhuizen, J. H. (2008) Structural characterization of oligosaccharides in the milk of an African elephant (Loxodonta africana africana). Comp. Biochem. Physiol. B Biochem. Mol. Biol. 150, 74-84. DOI ScienceOn
33	Uemura, Y., Asakuma, S., Yon, L., Saito, T., Fukuda, K., Arai, I. and Urashima, T. (2006) Structural determination of the oligosaccharides in the milk of an Asian elephant (Elephas maximus). Comp. Biochem. Physiol. A Mol. Integr. Physiol. 145, 468-478. DOI ScienceOn
34	Uemura, Y., Takahashi, S., Senda, A., Fukuda, K., Saito, T., Oftedal, O. T. and Urashima, T. (2009) Chemical characterization of milk oligosaccharides of a spotted hyena (Crocuta crocuta). Comp. Biochem. Physiol. A Mol. Integr. Physiol. 152, 158-161. DOI ScienceOn
35	Tao, N., Wu, S., Kim, J., An, H. J., Hinde, K., Power, M. L., Gagneux, P., German, J. B. and Lebrilla, C. B. (2011) Evolutionary glycomics: characterization of milk oligosaccharides in primates. J. Proteome Res. 10, 1548-1557. DOI ScienceOn
36	Zivkovic, A. M., German, J. B., Lebrilla, C. B. and Mills, D. A. (2011) Human milk glycobiome and its impact on the infant gastrointestinal microbiota. Proc. Natl. Acad. Sci. U.S.A. 108(Suppl 1), 4653-4658. DOI ScienceOn
37	Newburg, D. S., Ruiz-Palacios, G. M. and Morrow, A. L. (2005) Human milk glycans protect infants against enteric pathogens. Annu. Rev. Nutr. 25, 37-58. DOI ScienceOn
38	Morrow, A. L., Meinzen-Derr, J., Huang, P., Schibler, K. R., Cahill, T., Keddache, M., Kallapur, S. G., Newburg, D. S., Tabangin, M., Warner, B. B. and Jiang, X. (2011) Fucosyltransferase 2 non-secretor and low secretor status predicts severe outcomes in premature infants. J. Pediatr. 158, 745-751. DOI ScienceOn
39	Morrow, A. L., Ruiz-Palacios, G. M., Altaye, M., Jiang, X., Guerrero, M. L., Meinzen-Derr, J. K., Farkas, T., Chaturvedi, P., Pickering, L. K. and Newburg, D. S. (2004) Human milk oligosaccharide blood group epitopes and innate immune protection against campylobacter and calicivirus diarrhea in breastfed infants. Adv. Exp. Med. Biol. 554, 443-446. DOI
40	Wang, B. (2009) Sialic acid is an essential nutrient for brain development and cognition. Annu. Rev. Nutr. 29, 177-222. DOI ScienceOn
41	Hong, P., Ninonuevo, M. R., Lee, B., Lebrilla, C. and Bode, L. (2009) Human milk oligosaccharides reduce HIV- 1-gp120 binding to dendritic cell-specific ICAM3-grabbing non-integrin (DC-SIGN). Br. J. Nutr. 101, 482-486.
42	Kindberg, E., Hejdeman, B., Bratt, G., Wahren, B., Lindblom, B., Hinkula, J. and Svensson, L. (2006) A nonsense mutation (428G ${\rightarrow}$ A) in the fucosyltransferase FUT2 gene affects the progression of HIV-1 infection. AIDS 20, 685-689. DOI ScienceOn
43	Urashima, T., Kobayashi, M., Asakuma, S., Uemura, Y., Arai, I., Fukuda, K., Saito, T., Mogoe, T., Ishikawa, H. and Fukui, Y. (2007) Chemical characterization of the oligosaccharides in Bryde's whale (Balaenoptera edeni) and Sei whale (Balaenoptera borealis lesson) milk. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 146, 153-159. DOI ScienceOn
44	Urashima, T., Odaka, G., Asakuma, S., Uemura, Y., Goto, K., Senda, A., Saito, T., Fukuda, K., Messer, M. and Oftedal, O. T. (2009) Chemical characterization of oligosaccharides in chimpanzee, bonobo, gorilla, orangutan, and siamang milk or colostrum. Glycobiology 19, 499-508. DOI ScienceOn
45	Stepans, M. B., Wilhelm, S. L., Hertzog, M., Rodehorst, T. K., Blaney, S., Clemens, B., Polak, J. J. and Newburg, D. S. (2006) Early consumption of human milk oligosaccharides is inversely related to subsequent risk of respiratory and enteric disease in infants. Breastfeed. Med. 1, 207-215. DOI
46	Le Pendu, J., Ruvoen-Clouet, N., Kindberg, E. and Svensson, L. (2006) Mendelian resistance to human norovirus infections. Semin. Immunol. 18, 375-386. DOI ScienceOn
47	Thurl, S., Henker, J., Siegel, M., Tovar, K. and Sawatzki, G. (1997) Detection of four human milk groups with respect to Lewis blood group dependent oligosaccharides. Glycoconj. J. 14, 795-799. DOI
48	Wu, S., Tao, N., German, J. B., Grimm, R. and Lebrilla, C. B. (2010) Development of an annotated library of neutral human milk oligosaccharides. J. Proteome Res. 9, 4138-4151. DOI ScienceOn
49	Kobata, A. (2010) Structures and application of oligosaccharides in human milk. Proc. Jpn. Acad. Ser. B Phys. Biol. Sci. 86, 731-747. DOI ScienceOn
50	Marino, K., Lane, J. A., Abrahams, J. L., Struwe, W. B., Harvey, D. J., Marotta, M., Hickey, R. M. and Rudd, P. M. (2011) Method for milk oligosaccharide profiling by 2-aminobenzamide labeling and hydrophilic interaction chromatography. Glycobiology 21, 1317-1330. DOI ScienceOn
51	Blank, D., Gebhardt, S., Maass, K., Lochnit, G., Dotz, V., Blank, J., Geyer, R. and Kunz, C. (2011) High-throughput mass finger printing and Lewis blood group assignment of human milk oligosaccharides. Anal. Bioanal. Chem. 401, 2495-2510. DOI ScienceOn
52	Newburg, D. S., Ruiz-Palacios, G. M., Altaye, M., Chaturvedi, P., Meinzen-Derr, J., Guerrero Mde, L. and Morrow, A. L. (2004) Innate protection conferred by fucosylated oligosaccharides of human milk against diarrhea in breastfed infants. Glycobiology 14, 253-263. DOI
53	Kobata, A. (1992) Structures and functions of the sugar chains of glycoproteins. Eur. J. Biochem. 209, 483-501. DOI ScienceOn
54	Oriol, R., Le Pendu, J. and Mollicone, R. (1986) Genetics of ABO, H, Lewis, X and related antigens. Vox Sanguinis 51, 161-171. DOI ScienceOn
55	Urashima, T., Saito, T., Nakamura, T. and Messer, M. (2001) Oligosaccharides of milk and colostrum in non-human mammals. Glycoconj. J. 18, 357-371. DOI ScienceOn
56	Fukuda, K., Yamamoto, A., Ganzorig, K., Khuukhenbaatar, J., Senda, A., Saito, T. and Urashima, T. (2010) Chemical characterization of the oligosaccharides in Bactrian camel (Camelus bactrianus) milk and colostrum. J. Dairy Sci. 93, 5572-5587. DOI ScienceOn
57	Coppa, G. V., Bruni, S., Morelli, L., Soldi, S. and Gabrielli, O. (2004) The first prebiotics in humans: human milk oligosaccharides. J. Clin. Gastroenterol. 38, S80-83. DOI ScienceOn
58	Coppa, G. V., Zampini, L., Galeazzi, T. and Gabrielli, O. (2006) Prebiotics in human milk: a review. Dig. Liver Dis. 38(Suppl 2), S291-294. DOI ScienceOn
59	Barboza, M., Sela, D. A., Pirim, C., Locascio, R. G., Freeman, S. L., German, J. B., Mills, D. A. and Lebrilla, C. B. (2009) Glycoprofiling bifidobacterial consumption of galacto-oligosaccharides by mass spectrometry reveals strain-specific, preferential consumption of glycans. Appl. Environ. Microbiol. 75, 7319-7325. DOI ScienceOn
60	Nakamura, T., Urashima, T., Mizukami, T., Fukushima, M., Arai, I., Senshu, T., Imazu, K., Nakao, T., Saito, T., Ye, Z., Zuo, H. and Wu, K. (2003) Composition and oligosaccharides of a milk sample of the giant panda, Ailuropoda melanoleuca. Comp. Biochem. Physiol. B Biochem. Mol. Biol. 135, 439-448. DOI ScienceOn
61	Zhang, J., Schubothe, K., Li, B., Russell, S. and Lebrilla, C. B. (2005) Infrared multiphoton dissociation of O-linked mucin-type oligosaccharides. Anal. Chem. 77, 208-214. DOI ScienceOn
62	Pfenninger, A., Karas, M., Finke, B. and Stahl, B. (2002) Structural analysis of underivatized neutral human milk oligosaccharides in the negative ion mode by nano-electrospray MS(n) (part 1: methodology). J. Am. Soc. Mass Spectrom. 13, 1331-1340. DOI ScienceOn
63	Han, L. and Costello, C. E. (2011) Electron transfer dissociation of milk oligosaccharides. J. Am. Soc. Mass Spectrom. 22, 997-1013. DOI ScienceOn
64	Viverge, D., Grimmonprez, L., Cassanas, G., Bardet, L. and Solere, M. (1990) Variations in oligosaccharides and lactose in human milk during the first week of lactation. J. Pediatr. Gastroenterol. Nutr. 11, 361-364. DOI
65	Coppa, G. V., Gabrielli, O., Pierani, P., Catassi, C., Carlucci, A. and Giorgi, P. L. (1993) Changes in carbohydrate composition in human milk over 4 months of lactation. Pediatrics 91, 637-641.
66	Kunz, C., Rudloff, S., Baier, W., Klein, N. and Strobel, S. (2000) Oligosaccharides in human milk: structural, functional, and metabolic aspects. Annu. Rev. Nutr. 20, 699-722. DOI ScienceOn
67	Pfenninger, A., Karas, M., Finke, B. and Stahl, B. (2002) Structural analysis of underivatized neutral human milk oligosaccharides in the negative ion mode by nano-electrospray MS(n) (part 2: application to isomeric mixtures). J. Am. Soc. Mass Spectrom. 13, 1341-1348. DOI ScienceOn
68	Wuhrer, M., Deelder, A. M. and van der Burgt, Y. E. (2011) Mass spectrometric glycan rearrangements. Mass Spectrom. Rev. 30, 664-680. DOI ScienceOn
69	Hua, S., An, H. J., Ozcan, S., Ro, G. S., Soares, S., DeVere-White, R. and Lebrilla, C. B. (2011) Comprehen.- sive native glycan profiling with isomer separation and quantitation for the discovery of cancer biomarkers. Analyst 136, 3663-3671. DOI ScienceOn
70	Hua, S., Lebrilla, C. and An, H. J. (2011) Application of nano-LC-based glycomics towards biomarker discovery. Bioanalysis 3, 2573-2585. DOI ScienceOn
71	Blank, D., Dotz, V., Geyer, R. and Kunz, C. (2012) Human milk oligosaccharides and Lewis blood group: individual high-throughput sample profiling to enhance conclusions from functional studies. Adv. Nutr. 3, 440S-449S DOI
72	Newburg, D. S., Ruiz-Palacios, G. M., Altaye, M., Chaturvedi, P., Guerrero, M. L., Meinzen-Derr, J. K. and Morrow, A. L. (2004) Human milk alphal,2-linked fucosylated oligosaccharides decrease risk of diarrhea due to stable toxin of E. coli in breastfed infants. Adv. Exp. Med. Biol. 554, 457-461. DOI
73	Ninonuevo, M., An, H., Yin, H., Killeen, K., Grimm, R., Ward, R., German, B. and Lebrilla, C. (2005) Nanoliquid chromatography-mass spectrometry of oligosaccharides employing graphitized carbon chromatography on microchip with a high-accuracy mass analyzer. Electrophoresis 26, 3641-3649. DOI ScienceOn
74	Li, B., An, H. J., Hedrick, J. L. and Lebrilla, C. B. (2009) Infrared multiphoton dissociation mass spectrometry for structural elucidation of oligosaccharides. Methods Mol. Biol. 534, 23-35. DOI ScienceOn
75	Wu, S., Grimm, R., German, J. B. and Lebrilla, C. B. (2011) Annotation and structural analysis of sialylated human milk oligosaccharides. J. Proteome Res. 10, 856-868. DOI ScienceOn
76	Anraku, T., Fukuda, K., Saito, T., Messer, M. and Urashima, T. (2012) Chemical characterization of acidic oligosaccharides in milk of the red kangaroo (Macropus rufus). Glycoconj. J. 29, 147-156. DOI ScienceOn
77	Taufik, E., Fukuda, K., Senda, A., Saito, T., Williams, C., Tilden, C., Eisert, R., Oftedal, O. and Urashima, T. (2012) Structural characterization of neutral and acidic oligosaccharides in the milks of strepsirrhine primates: greater galago, aye-aye, Coquerel's sifaka and mongoose lemur. Glycoconj. J. 29, 119-134. DOI ScienceOn
78	Amano, J., Osanai, M., Orita, T., Sugahara, D. and Osumi, K. (2009) Structural determination by negative-ion MALDI-QIT-TOFMSn after pyrene derivatization of variously fucosylated oligosaccharides with branched decaose cores from human milk. Glycobiology 19, 601-614. DOI ScienceOn
79	Suzuki, Y., Suzuki, M., Ito, E., Ishii, H., Miseki, K. and Suzuki, A. (2005) Convenient and rapid analysis of linkage isomers of fucose-containing oligosaccharides by matrix- assisted laser desorption/ionization quadrupole ion trap time-of-flight mass spectrometry. Glycoconj. J. 22, 427-431. DOI
80	Li, B., Russell, S. C., Zhang, J., Hedrick, J. L. and Lebrilla, C. B. (2011) Structure determination by MALDI-IRMPD mass spectrometry and exoglycosidase digestions of O-linked oligosaccharides from Xenopus borealis egg jelly. Glycobiology 21, 877-894. DOI ScienceOn
81	Royle, L., Mattu, T. S., Hart, E., Langridge, J. I., Merry, A. H., Murphy, N., Harvey, D. J., Dwek, R. A. and Rudd, P. M. (2002) An analytical and structural database provides a strategy for sequencing O-glycans from microgram quantities of glycoproteins. Anal. Biochem. 304, 70-90. DOI ScienceOn

Reference

	Bianca Rebelo Lopes. (2016) Journal of Pharmaceutical and Biomedical Analysis Bioanalytical challenge: A review of environmental and pharmaceuticals contaminants in human milk / 130 , 318
1	Olivia Ballard. (2013) Pediatric Clinics of North America Human Milk Composition / 60 (1) , 49
5	Sercan Karav. (2015) Biotechnology Progress Characterizing the release of bioactiveN-glycans from dairy products by a novel endo-β-N-acetylglucosaminidase / 31 (5) , 1331
	Wen-Li Wang. (2017) Food Chemistry Comparison of anti-pathogenic activities of the human and bovine milk N -glycome: Fucosylation is a key factor / 235 , 167
3	David J. Harvey. (2017) Mass Spectrometry Reviews Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update for 2011-2012 / 36 (3) , 255
7	S. Qu. (2016) Journal of Dairy Science A profile of sphingolipids and related compounds tentatively identified in yak milk / 99 (7) , 5083
1	Alline R. Pacheco. (2015) Annual Review of Animal Biosciences The Impact of the Milk Glycobiome on the Neonate Gut Microbiota / 3 (1) , 419
12	Tong Zhang. (2015) PLOS ONE Changes in the Milk Metabolome of the Giant Panda (Ailuropoda melanoleuca) with Time after Birth – Three Phases in Early Lactation and Progressive Individual Differences / 10 (12) , e0143417
12	Esther Castanys-Munoz. (2013) Nutrition Reviews 2′-fucosyllactose: an abundant, genetically determined soluble glycan present in human milk / 71 (12) , 773
9	A. Marcobal. (2013) Glycobiology A refined palate: Bacterial consumption of host glycans in the gut / 23 (9) , 1038
6	Fabio Galeotti. (2014) ELECTROPHORESIS Capillary electrophoresis separation of human milk neutral and acidic oligosaccharides derivatized with 2-aminoacridone / 35 (6) , 811
	Jasmine C. C. Davis. (2017) Scientific Reports Growth and Morbidity of Gambian Infants are Influenced by Maternal Milk Oligosaccharides and Infant Gut Microbiota / 7 , 40466
16	Robert Kottler. (2013) ELECTROPHORESIS Development of a high-throughput glycoanalysis method for the characterization of oligosaccharides in human milk utilizing multiplexed capillary gel electrophoresis with laser-induced fluorescence detection / 34 (16) , 2323
9	Jasmine C. C. Davis. (2016) Molecular & Cellular Proteomics Identification of Oligosaccharides in Feces of Breast-fed Infants and Their Correlation with the Gut Microbial Community / 15 (9) , 2987
11	F. Javier Moreno. (2014) ELECTROPHORESIS Analysis, structural characterization, and bioactivity of oligosaccharides derived from lactose / 35 (11) , 1519
	Mark A. Underwood. (2014) Pediatric Research Bifidobacterium longum subspecies infantis: champion colonizer of the infant gut /
	Lucia Monti. (2015) Journal of Chromatography A Capillary electrophoresis of sialylated oligosaccharides in milk from different species / 1409 , 288
1	Silvia Sorbolini. (2016) Genetics Selection Evolution Use of canonical discriminant analysis to study signatures of selection in cattle / 48 (1)
7	Jingyu Yan. (2017) Anal. Methods Chromatographic methods for the analysis of oligosaccharides in human milk / 9 (7) , 1071
4	Josef Neu. (2014) Clinics in Perinatology Probiotics and Necrotizing Enterocolitis / 41 (4) , 967
	Stéphanie Oursel. (2017) Journal of Chromatography B Comparative analysis of native and permethylated human milk oligosaccharides by liquid chromatography coupled to high resolution mass spectrometry /
18606768	(2019) Biotechnology Journal Enzymatic Cascade Synthesis Provides Novel Linear Human Milk Oligosaccharides as Reference Standards for xCGE-LIF Based High-Throughput Analysis / (18606768)
11	(2017) Nutrition Reviews Systematic review of the concentrations of oligosaccharides in human milk / 75 (11) , 920
1	(2018) Annual Review of Food Science and Technology Milk Glycans and Their Interaction with the Infant-Gut Microbiota / 9 (1) , 429
1	(2018) Scientific Reports Characterization of porcine milk oligosaccharides over lactation between primiparous and multiparous female pigs / 8 (1)